Chukka Boots, Denim Jackets, & Shoe Versatility


Here’s what you missed on the most recent Style & Direction bi-weekly stream!

This week features EthanSpencerMJKiyoshi, Aldous, Ivan, HWilberg (his first time!), and Jason.

On the Chukka/Desert Boot

On a casual Wednesday stream, the boys and I discovered that Uniqlo now has a chukka boot on its roster of affordable Americana. It’s nothing spectacular and while none of us are going to be buying it anytime soon, it did launch us into a discussion on the chukka/desert boot itself.

As I wrote about in this old article, this boot is one that seems to be a basic choice (most of us are past that stage) but it’s one that we sometimes come back to in order to play into it’s simple ivy-trad aesthetic. It’s perfect for casual tailoring (like cotton suits) but the real vibe comes with the variations in design. Do you like the derby-esque unlined ones from Alden? Are you a fan of the rounded Astorflex? Or is the sleek, chisel-toe from Loake more your speed? We discuss it all.

Initial Discussion on the Denim Jacket

Aldous always loves to present topics that we’re planning on doing in the future- the first was the desert boot and now it’s the denim jacket. This is something that has been mysteriously lacking from the blog and it’s mainly because I haven’t quite figured out how to wear it; the same could be said for Spencer. Leaning into the rugged 60s-70s vibe is still pretty new to us and as a result, we haven’t formalized thoughts on our denim jackets.

We have a bit of a primer on the subject, with the boys stating what types they prefer: I like my Lee 101J while Spencer likes a Type-2. We also get into why some jackets are too long and why a Type-3 is a no-go (it’s too basic).

On Pocket Styles

I don’t know how we got here, but our conversation went to trouser pocket styles. It’s pretty clear that we don’t like on-seam pockets but in an oddly anti-60s tangent, Spencer and Kiyoshi reveal that they don’t like frog mouth pockets! Very interesting snippet.

What Makes a Versatile Shoe?

This one was a big topic that I was excited to bring on Henrik for. I couldn’t even cut it down into small pieces- we all jumped around a bit on this very interesting subject.

Initially posited by Chuck in our Discord, we were to discuss what a “versatile shoe” really is and how we rationalize it in our head. For my pals who live in Los Angeles and seldom have to walk anywhere, a shoe is mainly for style. For the guys who have to use public transportation and walk everywhere (aka, anywhere but LA), comfort and protection against the elements take a bit more precedence. Perhaps that is the reason why I tend to love wearing loafers, even if I never want to relive the death my feet experienced during the big 2018 NYC trip.

On a tangent, Henrik and I speak a bit about “forcing versatility”. By this, I mean that at a certain point, once your style is developed enough, you use your taste to determine what truly works with any outfit you create. It’s less about wearing something inoffensive and plain (like a white sneaker) but instead about what footwear you like that says something about you. That’s the main reason why I like wearing tassel loafers with everything, from formal to casual wear: it provides a louche feel that makes tailoring easier and rugged outfits a bit edgier.

It’s a great roundtable that you should listen to in its entirety. Or at least just enjoy MJ’s experience with the COD: Black Ops beta.

Our Number One Shoe

Before we started a game of Among Us, I briefly asked everyone what their No. 1 shoe pick would be, irrespective of context. I don’t think that changed what Spencer, MJ, and I talked about in the roundtable discussion, but it certainly did for the other guys, who were free to make this decision outside of harsh snowy winters.

What shoe would you pick? Let me know by commenting below.

Don’t forget to support us on Patreon to get some extra content and access to our exclusive Discord. Catch us streaming on Twitch every Wednesday and Saturday or watch the clips on Youtube.

Oh and don’t forget, we do a podcast every two weeks!


StyleandDirection | EthanMWong | SpencerDSO

The Podcast is produced by MJ and Matthew.

Big thank you to our top tier Patrons (the SaDCast Fanatics): Seth Peterson, Austin Malott, Eric Hall, Philip Gregard, Shane Curry, and Audrey Jessica.

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